Sahil Lavingia
Information Technology Specialist at Internal Revenue Service
About
I founded Gumroad and ran it for 14 years. Now I build taxpayer-facing tools at the IRS.
Experiences
- Information Technology Specialist at Internal Revenue ServiceWent from running Gumroad to working tech at the IRS
The IRS added online accounts in 2025 and keeps adding features. I think every taxpayer should have one.
- FlexileBuilding a way to pay contractors in equity
It came from how Gumroad pays freelancers. We're profitable with no VC and hit 45 customers in September.
- Silicon Valley → UtahLeft Silicon Valley for Utah after feeling like a failure
In Utah people asked what I did. When I said I'd failed to build a billion-dollar company, they were baffled.
- Founder & CEO at GumroadLaid off 75% of my team, then rebuilt with freelancers
After failing to raise a Series B, I hired contractors who saved the company. In 2023 we netted $8.9M.
- Founder & CEO at GumroadTweeted a billion-dollar idea, built it in a weekend
It was one 2,700-line Python file. About 50,000 people saw it on day one, but almost no one used it.
- Software Engineer and Designer at PinterestLanded Pinterest's iPhone app through a Hacker News post
I built Pinterest for iPhone by myself at 18, starting on a $4,000 invoice. I never vested my 0.75% stake.
- New York → SingaporeGrew up in Singapore, living off my apps by 17
Born in New York, raised in Singapore. I built 20 to 30 apps, including a cab-hailing app before Uber.
- ProfessionalWrote a book on unlearning the unicorn chase
It grew out of my 2019 essay on failing to build a billion-dollar company. I also taught it in 6-week cohorts.